Ethyl Acetate → HCID 22597432, compound

HRID 1760224Notes

Reaction equation

Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:11][C:12]1[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[N:16][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O.O>[CH3:19][O:18][C:15]1[N:16]=[CH:17][C:12]([NH:11][C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of 15 g of 2-chloro-3-nitropyridine, 11.7 g of 5-amino-2-methoxypyridine and 26.1 g of potassium carbonate in 150 mL dimethylformamide was stirred at room temperature for 4 hours and 25 minutes and further stirred at 70° C. for 3 hours and 10 minutes. Ethyl acetate and water were added to the reaction mixture, and the mixture was extracted once with ethyl acetate. The organic layer was washed 3 times with a saturated aqueous ammonium chloride solution and once with brine, and dried over sodium sulfate. The residue was purified crudely by short-column chromatography. From and the resulting black brown oil was extracted with diethyl ether to give 9.10 g of the title compound as reddish brown crystals (39% y.). (2) N2-(6-Methoxy-3-pyrdyl)-2,3-pyridinediamine

Workup

extractionthe mixture was extracted once with ethyl acetate
washThe organic layer was washed 3 times with a saturated aqueous ammonium chloride solution
dry with materialonce with brine, and dried over sodium sulfate
customThe residue was purified crudely by short-column chromatography
extractionFrom and the resulting black brown oil was extracted with diethyl ether

Sources & evidence

ORD record: ord-67a7a8688f514914a9405b28d6f6273b
Source dataset: uspto-grants-2005_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06841549B1

Reaction notes

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